Water → HCID 21190257, compound

HRID 619528Notes

Reaction equation

HRID 619528 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[N:9]3[C:10]=1[NH:11][C:12](=[O:13])[C:8]3=[CH:7][CH:6]=[CH:5]2.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].O>CN(C=O)C>[C:23]1(=[O:32])[N:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:11]2[C:10]3=[C:2]([CH3:1])[N:3]=[C:4]4[CH:5]=[CH:6][CH:7]=[C:8]([N:9]34)[C:12]2=[O:13])[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]12

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 136770N-(5-Bromopentyl)phthalimideHCID 21190144HCID 21190144, compound

Product 1

HCID 21190257HCID 21190257, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 277 mg (1.60 mmol) of 3,4-dihydro-2-methyl-1,3,7b-triazacyclopent[cd]inden-4-one in 3 ml of DMF was added, while stirring under ice-cooling, 77 mg (1.93 mmol) of 60% sodium hydride (dispersion in oil). The mixture was stirred for 15 minutes at the same temperature. To the reaction mixture was added 521 mg (1.76 mmol) of N-(5-bromopentyl)phthalimide. The mixture was stirred for one hour at 110° C. After cooling, the reaction mixture was poured into water, and extracted with ethyl acetate. The extract solution was washed with an aqueous saline solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to afford 410 mg of the desired compound (66.0%, a pale brown solid).

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringThe mixture was stirred for 15 minutes at the same temperature
  4. stirringThe mixture was stirred for one hour at 110° C
  5. temperatureAfter cooling
  6. extractionextracted with ethyl acetate
  7. washThe extract solution was washed with an aqueous saline solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off
  10. customthe residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1)

Sources & evidence

ORD record
ord-0106c7cef4504fa4ab500e1aac327dc4
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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